OVERVIEW

The role of organic chemistry in the field of Materials Science has become increasingly prominent, driven by the design and synthesis of innovative organic materials with diverse properties and functions. As such, a foundational understanding of organic chemistry is essential for future materials scientists.

The course is structured to emphasize conceptual understanding and critical thinking, rather than the mere memorization of facts.

AIMS AND CONTENT

LEARNING OUTCOMES

The aim of the course is to acquire foundational knowledge of the nomenclature, structure, and reactivity of the main classes of organic compounds; and to develop practical skills related to basic experimental procedures.

AIMS AND LEARNING OUTCOMES

At the end of the course, the student will have acquired:

1 – Knowledge and understanding

The student will know and understand the fundamentals of organic chemistry, including molecular structure, major functional groups, nomenclature, reactivity of organic compounds, and associated reaction mechanisms. The student will also be familiar with some practical aspects of the subject.

2 – Applying knowledge and understanding

The student will be able to apply both theoretical and practical knowledge to:

(i) deduce the structure of an organic molecule from its name and vice versa,

(ii) predict the chemical behavior of organic compounds based on their structure,

(iii) interpret experimental results obtained during laboratory activities.

3 – Making judgements

The student will be able to identify appropriate conditions to carry out specific structural modifications on organic compounds. They will also be able to analyze chemical structures in order to select the most suitable purification technique.

4 – Communication skills

The student will be able to clearly and accurately communicate acquired knowledge using appropriate scientific language, and to present experimental data in a clear and organized manner. Interpersonal communication will be encouraged, particularly during classroom and/or laboratory exercises.

5 – Learning skills

The student will have developed the ability to independently use the foundational knowledge acquired to continue exploring and deepening their understanding of the subject.

PREREQUISITES

A solid understanding of General and Inorganic Chemistry is a necessary prerequisite and should be ensured by the student prior to undertaking this course.

TEACHING METHODS

The course is delivered through both classroom lectures and laboratory sessions. During lectures, individual and/or group exercises will be conducted, including the use of interactive tools such as Wooclap.

Class attendance is not mandatory, but it is strongly recommended.

Laboratory sessions (20 hours – 5 experiments), on the other hand, are compulsory. Students will be required to complete mandatory preparatory quizzes before each laboratory session. A written lab report must be submitted via Aulaweb within two weeks after the final lab session. The report will be reviewed and graded by the instructor. Since experiments will be carried out in pairs, only one report per pair is required; however, students are encouraged to collaborate fully in writing it.

Supplementary exercises to support preparation for the oral exam will be made available on Aulaweb. These exercises are also useful for student self-assessment.

SYLLABUS/CONTENT

1) Introductory Concepts

· 1.1 Introduction

· 1.2 Chemical Bonding in Organic Compounds

o 1.2.1 Review of electronic configuration; definition of valence shell.

o 1.2.2 Lewis structures of molecules. Noble gas rule. Kekulé formulas.

o 1.2.3 Electronegativity: covalent and ionic bonds.

o 1.2.4 Charged molecules: determination of formal charge.

o 1.2.5 Resonance. Double-headed arrows.

o 1.2.6 Molecular shape. Definition of bond angle. Use of VSEPR theory to predict bond angles.

o 1.2.7 Molecular orbital theory. Concept of hybrid orbitals. Sigma and pi bonds.

· 1.3 Alkanes

o 1.3.1 Molecular formula and structural formula. Constitutional isomerism. Chemodiversity of alkanes.

o 1.3.2 Classification of carbon atoms.

o 1.3.3 Nomenclature of alkanes. Names of some simple mono- and bivalent radicals.

o 1.3.4 Natural sources of alkanes.

o 1.3.5 Octane number.

o 1.3.6 Concept of functional groups.

· 1.4 Overview of Main Functional Groups with Elements of Nomenclature

o 1.4.1 Alkenes, alkynes, arenes, alcohols, phenols, carbonyl compounds, carboxylic acids, amines, ethers, esters, amides.

o 1.4.2 Priority of functional groups.

· 1.5 Non-bonding interactions and physical properties

· 1.6 Acid-base properties of organic compounds

o 1.6.1 Review of fundamental concepts on acids and bases.

o 1.6.2 Factors influencing acidity.

o 1.6.3 Acidity of alcohols, thiols, alkynes, phenols, carboxylic acids, amides.

o 1.6.4 Basicity of alcohols, aliphatic and aromatic amines, amides, guanidines.

2) Stereochemistry and Conformations

· 2.1 Diversity of two substances

· 2.2 Conformations

o 2.2.1 Conformations of ethane

o 2.2.2 Conformations of butane

o 2.2.3 Conformations of cycloalkanes

o 2.2.4 Conformations of cyclohexane

· 2.3 Types of stereoisomers

· 2.4 Representation with wedges and dashed lines

· 2.5 Chirality. Stereogenic centers

· 2.6 R/S notation

· 2.7 Compounds with two stereogenic carbons

· 2.8 Optical activity

· 2.9 Enantiomeric mixtures

· 2.10 Fischer projections

· 2.11 Equivalent stereogenic centers

· 2.12 Chemical properties of enantiomers

· 2.13 Chirality in the biological world

· 2.14 E/Z isomerism in alkenes

3) Generalities on Organic Reactions and Alkene Reactions

· 3.1 General concepts of thermodynamics and kinetics of reactions. Catalysis.

· 3.2 Classification of reactions

· 3.3 Reaction mechanisms. Nucleophiles and electrophiles.

· 3.4 Hydrogenation of alkenes

· 3.5 Electrophilic addition to double bonds – Markovnikov’s rule

o 3.5.1 Addition of hydrogen halides

o 3.5.2 Hydration

o 3.5.3 Addition of halogens

4) Aromatic Compounds

· 4.1 Benzene and aromaticity

· 4.2 Nomenclature of benzene derivatives

· 4.3 Electrophilic substitution reactions on benzene

o 4.3.1 General overview

o 4.3.2 Halogenation

o 4.3.3 Nitration

o 4.3.4 Friedel-Crafts alkylation with alkenes

o 4.3.5 Friedel-Crafts acylation

o 4.3.6 Sulfonation. Uses of sulfonates as detergents

o 4.3.7 Activating/deactivating and directing effects of substituents

· 4.4 Heteroaromatic compounds

o 4.4.1 Structure and names

o 4.4.2 Basic properties

5) Description of Laboratory Exercises

· 5.1 Crystallization

· 5.2 Distillation

· 5.3 Liquid-liquid extraction

· 5.4 Chromatography

6) Reactions of C=O Double Bonds

· 6.1 Nucleophilic additions to carbonyl compounds

o 6.1.1 General overview

o 6.1.2 Addition of water

o 6.1.3 Addition of alcohols. General concepts on substitution reactions

o 6.1.4 Addition of nitrogen nucleophiles: imines

· 6.2 Keto-enol tautomerism

· 6.3 Nucleophilic acyl substitutions

o 6.3.1 General concepts on nucleophilic acyl substitutions: thermodynamic and kinetic aspects. Reactivity of various carboxylic acid derivatives

o 6.3.2 Preparation and hydrolysis of acyl chlorides

o 6.3.3 Preparation and hydrolysis of anhydrides

o 6.3.4 Preparation and hydrolysis of esters

o 6.3.5 Preparation and hydrolysis of amides

· 6.4 Other carboxylic acid derivatives

o 6.4.1 Nitriles

o 6.4.2 Carbonic acid derivatives

o 6.4.3 Sulfonic acid derivatives

o 6.4.4 Inorganic oxyacid derivatives

· 6.5 Electrophilic reactions at the alpha carbon of carbonyl groups

o 6.5.1 Acidity at the alpha position of carbonyl groups

o 6.5.2 Aldol additions and crotonic condensations

7) Oxidations and Reductions of Major Organic Compounds

· 7.1 Calculation of oxidation numbers

· 7.2 Reductions/oxidations at carbon

o 7.2.1 Oxidation levels at carbon

o 7.2.2 General concepts on reductions and oxidations at carbon

o 7.2.3 Reduction of carbonyl compounds, carboxylic acids, and nitriles. Complex hydrides

o 7.2.4 Reductive amination

o 7.2.5 Oxidation of alcohols to carbonyls and carboxyls

o 7.2.6 Oxidation of alkenes – epoxidation, osmylation

· 7.3 Reduction of nitro derivatives

· 7.4 Sulfur derivatives. Disulfides

8) Nucleophilic Substitutions at Saturated Carbon and Eliminations

· 8.1 SN2 nucleophilic substitutions

o 8.1.1 General concepts. Stereospecificity

o 8.1.2 Importance of leaving group and nucleophile

o 8.1.3 Influence of substrate

o 8.1.4 Influence of reaction conditions

o 8.1.5 Competition with E2 reaction

o 8.1.6 Synthesis of alcohols from alkyl halides

o 8.1.7 Williamson synthesis of ethers

o 8.1.8 Synthesis of amines. Synthesis via azides

o 8.1.9 Alkylation of cyanides

· 8.2SN1 substitutions and E1 eliminations

· 8.3 Epoxide ring-opening reactions

9) Natural Substances

· 9.1 Carbohydrates

o 9.1.1 Structure and stereochemistry of major monosaccharides

o 9.1.2 Mutarotation

o 9.1.3 Glycosides

o 9.1.4 Disaccharides

o 9.1.5 Polysaccharides

· 9.2 Lipids

o 9.2.1 Triglycerides – Waxes

o 9.2.2 Phospholipids

· 9.3 Amino acids and peptides

o 9.3.1 Description of various proteinogenic amino acids

o 9.3.2 Stereochemistry of amino acids

o 9.3.3 Acid-base properties of amino acids

o 9.3.4 Peptides

· 9.4 Nucleic acids

10) Introduction to Radical Reactions

· 10.1 General overview

· 10.2 Oxygen as a radical oxidant

o 10.2.1 Autooxidation: mechanism

o 10.2.2 Cumene hydroperoxide

o 10.2.3 Benzylic oxidation

o 10.2.4 Autooxidation of ethers, aldehydes, unsaturated and polyunsaturated systems

o 10.2.5 Radical stabilizers

· 10.3 Quinones and hydroquinones

11) ADDITIONAL LESSONS

· 11.1 Reduction of alkyl halides: organometallic compounds

o 11.1.1 Preparations

o 11.1.2 Brønsted basicity properties

o 11.1.3 Reactions with aldehydes and ketones

o 11.1.4 Reactions with esters, nitriles, and carbon dioxide

· 11.2 Radical polymerizations

· 11.3 Radical halogenation of alkanes

· 11.4 Radical halogenation at benzylic and allylic positions

· 11.5 Synthetic applications of the E2 elimination reaction

· 11.6 Polymers

o 11.6.1 Polyesters

o 11.6.2 Polyamides

o 11.6.3 Bio-based polymers

LABORATORY EXERCISES

1. Distillation and crystallization

2. Liquid-liquid extraction

3. Chromatography

4. Synthesis of acetylsalicylic acid

5. Classical resolution of α-methylbenzylamine – polarimetry

RECOMMENDED READING/BIBLIOGRAPHY

Teaching materials are available on Aulaweb.

Students are advised to complement the provided materials with their own lecture notes; for this reason, attending classes is strongly recommended.

Consulting an Organic Chemistry textbook for non-chemistry majors may also be helpful (copies are available in the library). Some recommended titles include:

· W. H. Brown "Introduzione alla Chimica Organica", EdiSES

· J. McMurry "Fondamenti di Chimica Organica", Zanichelli

· J.G. Smith "Fondamenti di Chimica Organica", McGraw Hill

· L.G. Wade "Fondamenti di Chimica Organica", Piccin

· D. Klein, "Fondamenti di Chimica Organica", Pearson

· P. Y. Bruice, «Elementi di Chimica Organica», EdiSES

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

Lectures will begin as indicated in the academic calendar. Updates will also be posted on Aulaweb. Class Schedule: The timetable for this course is available via the Portale EasyAcademy, or the MyUniGe app

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The exam consists of an oral assessment covering the entire course program, aimed at evaluating the achievement of the learning objectives.

During the oral exam, students will be required to demonstrate their ability to write chemical formulas and equations, and to correctly describe the reactivity and properties of the various classes of molecules studied, as well as the laboratory techniques covered during the course.

* Students with disabilities or specific learning disorders (SLD) are reminded that, in order to request exam accommodations, they must follow the instructions provided at the following link: https://corsi.unige.it/corsi/11968/studenti-disabilita-dsa

ASSESSMENT METHODS

The assessment methods will prioritize the student's logical reasoning and problem-solving abilities over mere rote memorization. During the oral exam, the instructor will aim to guide the student toward a correct explanation, even in cases where the topic is not recalled in full, by encouraging reasoning based on fundamental principles and logic.

The oral exam will be used to assess whether the student has achieved the intended learning outcomes.

Students are advised, during their preparation, to practice writing chemical formulas and stoichiometric equations, as what is written on the board during the exam will carry equal weight to the oral explanation.

FURTHER INFORMATION

Classroom attendance is not mandatory, but it is strongly recommended.

In general, please refer to Aulaweb for all details and/or updates.